KR20220150833A - Organic compound and organoelectroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device including the same, and more specifically, to an organic electroluminescent device having long lifespan, high efficiency, and high color purity as a blue-based blue host/dopant system suitable for AM-OLED using the organic compound.

Description

Organic compound and organic electroluminescent device using the same

The present invention relates to a novel organic compound and an organic electroluminescent device including the same.

Organic light emitting devices (OLEDs) have a simpler structure than other flat panel display devices such as conventional liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), and have various advantages in the manufacturing process, It has excellent characteristics of high brightness and viewing angle, fast response speed, and low driving voltage, so it is being actively developed and commercialized to be used as a light source for flat panel displays such as wall-mounted TVs or backlights of displays, lighting, and billboards.

The first organic EL device was reported (C. W. Tang, S. A. Vanslyke, Applied Physics Letters, Volume 51, page 913, 1987) by C. W. Tang of Eastman Kodak, etc. When a voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form excitons, which are electron-hole pairs, and are converted into light by transferring the energy of the excitons to the light emitting material.

More specifically, the organic light emitting device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers between the two electrodes. At this time, the organic electroluminescent device is a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron transport layer (ETL) from the anode. It is stacked in the order of EIL (electron injection layer), and in order to increase the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) is added in front and behind the light emitting layer, respectively. can be included with

Most of the materials used in the organic layer of the organic electroluminescent device are pure organic materials or complex compounds in which organic materials and metals are complexed. It can be divided into injection materials and the like.

Here, as the hole injection material or the hole transport material, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. As an electron injection material or electron transport material, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used.

On the other hand, as the material of the light emitting layer, a material having a stable form in both oxidation and reduction states is preferable, and a material having high luminous efficiency converting excitons into light when they are formed is preferable. More specifically, the light emitting layer is composed of two materials, a host and a dopant, and the dopant must have high quantum efficiency, and the host material has a larger energy gap than the dopant material to facilitate energy transfer to the dopant. it is desirable Display used for TV, mobile, etc., realizes full color with three colors of red, green, and blue, and the light emitting layer is composed of red host/dopant, green host/dopant, and blue host/dopant, respectively. It consists of

Materials used as conventional blue dopants were mostly fluorescent molecules such as Perylene, Coumarine, Anthracene, and Pyrene. The width half the maximum) is wide, so there is a disadvantage in that pure blue light cannot be used in device manufacturing. This characteristic not only reduces the efficiency of blue color in the resonance structure of the device, but also is the main reason why it is difficult to utilize the deep blue section.

Recently, a literature using a boron-based dopant with a narrow emission spectrum and high device efficiency is published in Adv. Mater. 2016, 28, 2777-2781 and Angew. Chem. Int. Ed 2017, 56, 5087-5090 and disclosed in Korean Patent Publication No. 10-2016-0119683. In the case of the previously introduced boron-based blue dopant material, the boron atom is included in the center and is cyclized, and as a result, only the three-coordinate bond of boron is formed, and the molecular structure maintains a planar state.

Such a dopant having a planar structure has an advantage of being able to emit pure light because the energy level of the vibration mode of the molecule is similar and the emission spectrum and half width are narrowed.

(Non-Patent Document 1) Krebs, Frederik C., et al. "Synthesis, Structure, and Properties of 4, 8, 12- Trioxa-12c-phospha-4, 8, 12, 12c-tetrahydrodibenzo [cd, mn] pyrene, a Molecular Pyroelectric." Journal of the American Chemical Society 119.6 (1997): 1208-1216.

An object of the present invention is to provide a novel organic compound and an organic electroluminescent device including the same.

Another object of the present invention is to provide a novel compound that has a narrow emission spectrum and a full width at half maximum and can be used as a material for an emission layer as an organic compound.

Another object of the present invention is to provide a blue-based blue host/dopant system suitable for AM-OLED using the organic compound, and to provide an organic light emitting device with long lifespan, high efficiency and high color purity.

In order to achieve the above object, the present invention provides a compound represented by Formula 1 below:

[Formula 1]

here,

n is 0 or 1;

Y ₁ is B, N, P=0 or P=S;

X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of N, C(R ₂ ), B and Si(R ₃ ),

X ₃ to X ₅ are the same as or different from each other, and are each independently a single bond, N(R ₄ ), C(R ₅ )(R ₆ ), O, S, and Si(R ₇ )(R ₈ ) A group consisting of is selected from,

Cy ₁ to Cy ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms,

R ₁ to R ₈ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,

The substituents of Cy ₁ to Cy ₄ and R ₁ to R ₈ are the same as or different from each other, and are each independently selected from hydrogen, cyano group, nitro group, halogen group, hydroxyl group, alkyl group having 1 to 30 carbon atoms, and alkene having 2 to 30 carbon atoms. Nyl group, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms One selected from the group consisting of an alkyl group, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms It may be substituted with the above substituents, but is not limited to the above examples.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the one or more organic material layers includes the compound represented by Chemical Formula 1. provide a small

For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. However, the structure of the organic EL device is not limited thereto and may include a smaller number of organic material layers.

According to a preferred embodiment of the present invention, the organic material layer is a light emitting layer, and the light emitting layer may be characterized in that it includes the compound represented by the formula (1).

In the present invention, "hydrogen" is hydrogen, light hydrogen, deuterium or tritium.

In this specification, "halogen group" is fluorine, chlorine, bromine or iodine.

In the present invention, “alkyl” means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight-chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

In the present invention, "alkylthio" means the above-described alkyl group bonded through a sulfur linkage (-S-).

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluoryl, dimethylfluorenyl, and the like.

In the present invention, “heteroaryl” means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. can include Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, “alkoxy” may be straight chain, branched chain or cyclic chain. The number of carbon atoms in alkoxy is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be, but is not limited thereto.

As used herein, "aralkyl" refers to an aryl-alkyl group where aryl and alkyl are defined above. Preferred aralkyls include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl and naphthalenylmethyl. Attachment to the parent moiety is via an alkyl.

In the present invention, "arylamino group" means an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, "alkylamino group" means an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, “aralkylamino group” means an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, "heteroarylamino group" means an amine group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.

In the present invention, "heteroaralkyl group" means an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, “heterocycloalkyl” means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are N, O, S or Se is substituted with a heteroatom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present specification, "alicyclic compound" has the same meaning as "aliphatic hydrocarbon ring", and refers to a non-aromatic ring consisting of only carbon and hydrogen atoms.

In the present specification, "heteroalicyclic compound" refers to an alicyclic compound containing at least one heteroatom by replacing one or more carbon atoms of the "aliphatic hydrocarbon ring" with a heteroatom.

Examples of the “aromatic hydrocarbon ring” in the present specification include, but are not limited to, a phenyl group, a naphthyl group, an anthracenyl group, and the like.

In the present specification, "aliphatic heterocycle" means an aliphatic ring containing one or more of heteroatoms.

In the present specification, "aromatic heterocycle" means an aromatic ring containing one or more of heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, “concentration quenching” means that the luminous efficiency of a device decreases as the concentration of dopant molecules increases.

In the present specification, “boron-based element”, “boron-based compound”, and “boron-based dopant” refer to a boron (B) element having an atomic number of 5, a compound containing boron, or a dopant.

In this specification, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other. The substituent is hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, and a C6 to C30 alkenyl group. Aralkyl group of 30, aryl group of 5 to 30 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, heteroarylalkyl group of 3 to 30 carbon atoms, alkoxy group of 1 to 30 carbon atoms, alkylamino group of 1 to 30 carbon atoms, 6 to 30 carbon atoms It may be substituted with one or more substituents selected from the group consisting of an arylamino group of 30, an aralkylamino group of 6 to 30 carbon atoms, and a hetero arylamino group of 2 to 24 carbon atoms, but is not limited to the above examples.

In the present invention, "to form a ring by bonding with adjacent groups" means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof.

The present invention provides a novel compound that can be used as an emission layer material as an organic compound having a narrow emission spectrum and a full width at half maximum.

In addition, the present invention is a blue-based blue host/dopant system suitable for AM-OLED using the organic compound, and provides an organic light emitting device with long lifespan, high efficiency, and high color purity.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. However, the present invention may be embodied in many different forms and is not limited to the embodiments described herein.

The organic compound according to the present invention has a planar structure, minimizes the π-π mutual attraction of molecules in the molecule, and has almost similar energy levels of vibration modes of molecules, thereby providing a narrow emission spectrum and It has a full width at half maximum, and concentration quenching, which can occur when the compound is used as a dopant, can be suppressed.

The organic compound according to the present invention includes atoms providing a planar structure, such as boron-based elements, to prevent generation of excimers in molecules, and to increase the efficiency and lifespan of the device by increasing the electron density of the core and the stability of the dopant. can make it possible.

Specifically, it relates to a compound represented by Formula 1 below:

[Formula 1]

here,

n and m are the same as or different from each other and are each independently 0 or 1,

Y ₁ is B, N, P=0 or P=S;

X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of N, C(R ₂ ), B and Si(R ₃ ),

X ₃ to X ₅ are the same as or different from each other, and are each independently a single bond, N(R ₄ ), C(R ₅ )(R ₆ ), O, S, and Si(R ₇ )(R ₈ ) A group consisting of is selected from,

Cy ₁ to Cy ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms,

R ₁ to R ₈ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,

The substituents of Cy ₁ to Cy ₄ and R ₁ to R ₈ are the same as or different from each other, and are each independently selected from hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, and an alkene having 2 to 30 carbon atoms. Nyl group, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms One selected from the group consisting of an alkyl group, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms It may be substituted with the above substituents, but is not limited to the above examples.

The compound represented by Formula 1 may be a compound represented by Formula 2 or Formula 3 below:

[Formula 2]

[Formula 3]

here,

n, m, Y ₁ , X ₁ to X ₅ , Cy ₁ to Cy ₄ and R ₁ are as defined in Formula 1 above,

X ₆ and X ₇ are the same as or different from each other, and are each independently a single bond, N(R ₉ ), C(R ₁₀ ) (R ₁₁ ), O, S, and Si(R ₁₂ ) (R ₁₃ ). is selected from,

CY ₅ and CY ₆ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;

R ₉ to R ₁₃ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,

The substituents of Cy ₅ , Cy ₆ and R ₉ to R ₁₃ are the same as or different from each other, and are each independently selected from hydrogen, cyano group, nitro group, halogen group, hydroxy group, C1-30 alkyl group, and C2-30 alkene group. Nyl group, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms One selected from the group consisting of an alkyl group, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms It may be substituted with the above substituents, but is not limited to the above examples.

The compound represented by Formula 2 may be a compound represented by Formula 4 or Formula 5 below:

[Formula 4]

[Formula 5]

here,

n, m, Y ₁ , X ₁ to X ₆ , Cy ₁ , Cy _2, Cy ₅ and R ₁ are as defined in Formula 2 above;

o, p and q are the same as or different from each other, and each independently represents an integer from 0 to 4;

r is an integer from 0 to 2;

Z ₁ is selected from the group consisting of O, S, N(R ₁₈ ) and C(R ₁₉ )(R ₂₀ );

R ₁₄ to R ₂₀ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,

The substituents of R ₁₄ to R ₂₀ are the same as or different from each other, and are each independently hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a carbon atom 2 to 24 alkynyl group, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, and 1 to 30 carbon atoms may be substituted with one or more substituents selected from the group consisting of an alkoxy group, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms However, it is not limited to the above example.

The compound represented by Formula 3 may be a compound represented by Formula 6 below:

[Formula 6]

here,

n, m, Y ₁ , X ₁ to X ₇ , Cy ₁ , Cy _2, Cy _5, Cy ₆ and R ₁ are as defined in Formula 3 above,

s and t are the same as or different from each other, and are each independently an integer of 0 to 3,

R ₂₁ and R ₂₂ are the same as or different from each other, and are each independently hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom group. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,

The substituents of R ₂₁ and R ₂₂ are the same as or different from each other, and are each independently hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a carbon atom group having 2 to 24 carbon atoms. alkynyl group, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, and 1 to 30 carbon atoms may be substituted with one or more substituents selected from the group consisting of an alkoxy group, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms However, it is not limited to the above example.

The compound represented by Formula 1 according to the present invention may be represented by the following compounds, but is not limited thereto:

The compound represented by Chemical Formula 1 of the present invention can be usefully used as a dopant material for an emission layer. Specifically, the organic compound as a dopant material may provide an organic compound that is thermally stable and minimizes concentration quenching compared to conventional boron-based dopants.

The organic compound of the present invention can be usefully used as a material for forming a light emitting layer. In the above, the material for forming the light emitting layer may further include a material that is typically added when preparing the organic compound in a form required for use in forming the light emitting layer, such as a host material.

The material for forming the emission layer may be a material for a dopant.

The present invention provides an organic electroluminescent device including the compound represented by Formula 1 above.

In addition, the present invention relates to a material for forming a light emitting layer containing the above organic compound.

In the above, the material for forming the light emitting layer may further include a material that is typically added when preparing the organic compound in a form required for use in forming the light emitting layer, such as a host material.

In addition, the present invention is an organic electroluminescent device in which an organic thin film layer composed of one or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode,

It relates to an organic electroluminescent device characterized in that the light emitting layer contains the organic compound represented by Formula 1 alone or in combination of two or more.

The organic light emitting device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and an electron blocking layer, a hole blocking layer, etc. are further laminated as necessary. It can be.

Hereinafter, the organic electroluminescent device of the present invention will be described as an example. However, the content exemplified below does not limit the organic electroluminescent device of the present invention.

The organic light emitting device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked, Preferably, an electron blocking layer (EBL) may be further included between the anode and the light emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) may be further included between the cathode and the light emitting layer. In addition, a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer.

In the manufacturing method of the organic light emitting device according to the present invention, first, an anode is formed by coating a substrate surface with a material for an anode in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer (HIL) material is vacuum thermally deposited or spin-coated on the surface of the anode in a conventional manner to form a hole injection layer. Materials for the hole injection layer include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), and 4,4',4"-tris(3-methylphenyl). Amino) phenoxybenzene (m-MTDAPB), starburst amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu is exemplified.

A hole transport layer (HTL) material is vacuum thermally deposited or spin-coated on the surface of the hole injection layer in a conventional manner to form a hole transport layer. At this time, the hole transport layer material is bis (N- (1-naphthyl-n-phenyl)) benzidine (α-NPD), N, N'-di (naphthalen-1-yl) -N, N'-biphenyl -benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD).

A light-emitting layer (EML) material is vacuum thermally deposited or spin-coated on the surface of the hole transport layer in a conventional manner to form the light-emitting layer. At this time, as a single light emitting material or light emitting host material among the materials of the light emitting layer used, in the case of green, tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ), etc. may be used, and in the case of blue, Alq ₃ , CBP (4, 4'-N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicarbazole-biphenyl), PVK (poly(n-vinylcabazole), poly(n-vinylcarbazole)), ADN( 9,10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalene-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene , 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene, 3-tert-butyl -9,10-di (naphth-2yl) anthracene), E3, DSA (distyrylarylene, distyrylarylene), or a mixture of two or more thereof may be used, but is not limited thereto.

In the case of a dopant (Dopant) that can be used together with the light emitting host of the light emitting layer material, the compound of the present invention can be preferably used.

Optionally, an electron blocking layer (EBL) may be further formed between the hole transport layer and the light emitting layer.

An electron transport layer (ETL) material is vacuum thermally deposited or spin-coated on the surface of the light emitting layer in a conventional manner to form an electron transport layer. At this time, the electron transport layer material used is not particularly limited, and preferably tris(8-hydroxyquinolinolato) aluminum (Alq ₃ ) may be used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer together, diffusion of triplet excitons or holes into the electron transport layer can be prevented. .

Formation of the hole blocking layer may be carried out by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, it is not particularly limited, but preferably (8-hydroxyquinolinola To) lithium (Liq), bis(8-hydroxy-2-methylquinolinato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF, and the like can be used.

An electron injection layer (EIL) material is vacuum thermally deposited or spin-coated on the surface of the electron transport layer in a conventional manner to form an electron injection layer. In this case, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the material for the electron injection layer.

An anode is formed by vacuum thermally depositing a cathode material on the surface of the electron injection layer in a conventional manner.

At this time, the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like may be used. In addition, in the case of a top emission organic light emitting device, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

A capping layer (CPL) may be formed on the surface of the negative electrode by a conventional composition for forming a capping layer.

Hereinafter, methods for synthesizing the above compounds will be described below with representative examples. However, the method for synthesizing the compounds of the present invention is not limited to the methods exemplified below, and the compounds of the present invention may be prepared by methods exemplified below and methods known in the art.

[Synthesis Example 1: Preparation of Compound 1]

Synthesis of A1-1

27.94 g (100.0 mmol) of 3,6-di-tert-butyl-9H-carbazole and 48.84 g (135.0 mmol) of 1,3-dibro-5-iodobenzene and 0.57 g (3.0 mmol) of copper iodide 106.1 g (500.0 mmol) of potassium triphosphate and 4.56 g (40 mmol) of 1,2-cyclohexanediamine were put in 300 mL of 1,4-dioxane, and the mixture was stirred at 120° C. for 24 hours under a nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature, inorganic substances were filtered, and the solvent was removed by distillation under reduced pressure, and the organic layer was separated using water and chloroform. After removing water using MgSO4, the organic layer was filtered and distilled under reduced pressure to remove the solvent. The resulting solid was subjected to silica gel column chromatography (DCM/Hexane) to obtain 34.6 g of Compound A1-1 in a yield of 67.4%.

MS (MALDI-TOF) m/z: 513 [M]+

Synthesis of A1-2.

34.6 g (67.0 mmol) of starting material A1-1 and 37.83 g (147.4 mmol) of 6-tert-butyl-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole After adding 25.75 g (268.0 mmol) of sodium tert-butoxide and dissolving in 300 ml of toluene, stirring for 30 minutes in a nitrogen atmosphere, tri-tert-butylphosphine 1.07 g (5.3 mmol) and tris (dibenzylidene acetone) 2.45 g (2.6 mmol) of dipalladium (0) was added and refluxed at 100° C. for 12 hours. After completion of the reaction, after cooling to room temperature, the organic layer was extracted using 200 ml of water and 300 ml of dichloromethane, dried with MgSO4, distilled off the filtrate, purified by column chromatography, and recrystallized with hexane/dichloromethane to obtain the compound A1-2 34.8 g was obtained in 59.9% yield.

MS (MALDI-TOF) m/z: 865 [M]+

Synthesis of Compound 1

After putting 34.8 g (40.1 mmol) of starting material A1-2 in 350 mL of o-dichlorobenzene (1,2-dichlorobenzene), 15.22 mL (160.4 mmol) of boron tribromide was added. Thereafter, the mixture was stirred at 180° C. for 24 hours. After cooling the reaction mixture to room temperature, 27.94mL (160.4mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60°C for 2 hours. After cooling to room temperature and slowly adding methanol, the mixture was stirred for 30 minutes. After obtaining the precipitated solid by filtration, it was recrystallized from dichloromethane and acetone to obtain 13.3 g of Compound 1 in a yield of 37.6%.

MS (MALDI-TOF) m/z: 881 [M]+

[Synthesis Example 2: Preparation of Compound 33]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 9,9'-(5-(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)-1,3-phenyl 34.5% of 3.12 g of the compound 33 was prepared in the same manner as in Synthesis Example 1 , except that 8.9 g (10 mmol) of len) bis(3,6-di-tert-butyl-9H-carbazole) was used. obtained in yield.

MS (MALDI-TOF) m/z: 903 [M]+

[Synthesis Example 3: Preparation of Compound 71]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 3,5-bis(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)-N,N-bis(4- 2.32 g of the compound 71 was obtained in a yield of 26.2% in the same manner as in Synthesis Example 1 , except that 8.7 g (10 mmol) of tert-butylphenyl)aniline was used.

MS (MALDI-TOF) m/z: 883 [M]+

[Synthesis Example 4: Preparation of Compound 139]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 5-(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)-N1,N1,N3,N3-tetrakis( 3.31 g of the compound 20 was obtained in a yield of 36.4% using the same method as in Synthesis Example 1 , except that 8.9 g (10 mmol) of 4-tert-butylphenyl) benzene-1,3-diamine was used.

MS (MALDI-TOF) m/z: 907 [M]+

[Synthesis Example 5: Preparation of Compound 4]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 9,9'-(5-(3,6-dicyclohexyl-9H-carbazole-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a-dimethyl-2, 3,4,4a,9,9a-hexahydro-1H-carbazole) 24.3% yield of 2.27 g of Compound 4 using the same method as in Synthesis Example 1 , except that 9.2 g (10 mmol) was used. got it with

MS (MALDI-TOF) m/z: 933 [M]+

[Synthesis Example 6: Preparation of Compound 16]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 10-(3,5-bis(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)phenyl)-10H-phenoxy 2.20 g of the compound 16 was obtained in a yield of 28.0% using the same method as in Synthesis Example 1 , except that the photo was changed to 7.7 g (10 mmol).

MS (MALDI-TOF) m/z: 785 [M]+

[Synthesis Example 7: Preparation of Compound 36]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 3,6-di-tert-butyl-9-(3-(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl ) -5- (3,6-diphenyl-9H-carbazol-9-yl) phenyl) -9H-carbazole using the same method as in Synthesis Example 1 except for changing to 9.3 g (10 mmol) Thus, 3.63 g of the compound 36 was obtained in a yield of 38.4%.

MS (MALDI-TOF) m/z: 943 [M]+

[Synthesis Example 8: Preparation of Compound 72]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 3,5-bis(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)-N,N-bis(3- 2.65 g of the compound 72 was obtained in a yield of 29.9% using the same method as in Synthesis Example 1 , except that 8.7 g (10 mmol) of tert-butylphenyl)aniline was used.

MS (MALDI-TOF) m/z: 883 [M]+

[Synthesis Example 9: Preparation of Compound 148]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) N1-(biphenyl-3-yl)-N3-(biphenyl-4-yl)-5-(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H- Carbazol-9 (9aH) -yl) -N1- (3-cyclohexylphenyl) -N3- (4-cyclohexylphenyl) benzene-1,3-diamine 9.8g (10mmol) except for use Using the same method as in Synthesis Example 1 , 3.66 g of the compound 148 was obtained in a yield of 36.6%.

MS (MALDI-TOF) m/z: 999 [M]+

[Synthesis Example 10: Preparation of Compound 209]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 5-(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)-N1,N3-bis(3-tert-butyl Phenyl) -N1, N3-bis (4-tert-butylphenyl) benzene-1,3-diamine 8.9g (10mmol) was used, but the same method as in Synthesis Example 1 was used to obtain the compound 209 3.43 g was obtained in 37.7% yield.

MS (MALDI-TOF) m/z: 907 [M]+

[Synthesis Example 11: Preparation of Compound 109]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) N-(benzo[b]thiophen-3-yl)-N-(3,5-bis(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carba Compound 109 2.63 using the same method as in Synthesis Example 1 , except that sol-9 (9aH) -yl) phenyl) dibenzo [b, d] furan-3-amine was changed to 9.0 g (10 mmol). g was obtained in 28.6% yield.

MS (MALDI-TOF) m/z: 917 [M]+

[Synthesis Example 12: Preparation of Compound 140]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- Dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) was changed to 9.1 g (10 mmol) of Compound A12-1 , but using the same method as in Synthesis Example 1 2.74 g of the compound 140 was obtained in a yield of 39.1%.

MS (MALDI-TOF) m/z: 700 [M]+

[Synthesis Example 13: Preparation of Compound 20]

Starting material 9,9'-(5-(3,6-di-tert-butyl-9H-carbazol-9-yl)-1,3-phenylene)bis(6-tert-butyl-4a,9a- dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole) 3-(6-tert-butyl-4a,9a-dimethyl-2,3,4,4a-tetrahydro-1H-carbazol-9(9aH)-yl)-N,N-bis(4-tert-butyl Phenyl) -5- (3,6-di-tert-butyl-9H-carbazol-9-yl) aniline 8.9 g (10 mmol) was used in the same manner as in Synthesis Example 1 , except that 8.9 g (10 mmol) was used. 2.78 g of Compound 20 was obtained in a yield of 30.6%.

MS (MALDI-TOF) m/z: 905 [M]+

[Example 1: Manufacturing organic light emitting device]

The substrate on which ITO (100 nm), the anode of the organic light emitting device, was laminated was patterned by dividing it into cathode and anode regions and an insulating layer through a photo-lithograph process, and then the work function of the anode (ITO) ( The surface was treated with UV Ozone treatment and O2:N2 plasma for the purpose of increasing work-function and cleaning. HAT-CN was formed thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4 as a hole transport layer on the hole injection layer, 4'-diamine was vacuum deposited to form a thickness of 90 nm, and as an electron blocking layer (EBL) on the hole transport layer (HTL), N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9 '-fluorene] -2'-yl) phenyl) dibenzo [b, d] furan-4-amine was formed to a thickness of 15 nm. An emission layer (EML) having a thickness of 25 nm was formed on the electron blocking layer (EBL) by depositing α,β-AND as a host of the emission layer and simultaneously doping 2% of Compound 1 as a dopant.

2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and LiQ were added as an electron transport layer (ETL) thereon. 25 nm was deposited by mixing at a weight ratio of 1: 1, an electron injection layer was deposited on the electron transport layer, 1 nm was deposited, and aluminum was deposited to a thickness of 100 nm as a cathode. Thereafter, an organic light emitting device was manufactured by attaching a seal cap including a getter with a UV curable adhesive to protect the organic light emitting device from oxygen or moisture in the air.

[Examples 2 to 13: Manufacturing organic light emitting devices]

Except for compounds 33, 71, 139, 4, 16, 36, 72, 148, 209, 109, 140, and 20 instead of compound 1, an organic light emitting device was prepared using the same method as in Example 1. did

[Comparative Examples 1 and 2: Preparation of organic light emitting device]

An organic light emitting device was manufactured in the same manner as in Example 1, except for using the following compounds A and B instead of Compound 1 as dopants.

[Compound A]

[Compound B]

[Experimental Example: Analysis of Characteristics of Organic Electroluminescent Device]

A current of 10 mA/cm ² was applied to the organic light emitting devices prepared in Examples 1 to 13 and Comparative Examples 1 and 2 to measure electrical properties and lifespan was measured by driving with a constant current of 10 mA/cm ² .

The measurement results are shown in Table 1 below.

division dopant Driving voltage (V) efficiency color life span Cd/A Im/A EQE CIEx CIEy T95
(hrs) Example 1 compound 1 3.41 7.7 7.1 16.8 0.139 0.044 256 Example 2 compound 33 3.56 4.9 4.3 15.2 0.150 0.027 134 Example 3 compound 71 3.51 6.6 5.9 13.3 0.137 0.49 261 Example 4 compound 139 3.3 6.7 6.2 14.6 0.139 0.043 250 Example 5 compound 4 3.47 7.6 6.9 16.6 0.140 0.044 250 Example 6 compound 16 3.54 6.9 6.2 15.5 0.140 0.042 130 Example 7 compound 36 3.56 7.8 6.9 16.6 0.139 0.045 280 Example 8 compound 72 3.59 5.8 5.1 15.5 0.146 0.033 146 Example 9 compound 148 3.48 8.1 7.3 17.4 0.139 0.044 220 Example 10 compound 209 3.55 7.8 6.9 15.9 0.137 0.047 128 Example 11 compound 109 3.54 9.7 8.6 18.6 0.134 0.053 160 Example 12 compound 140 3.52 6.6 5.9 12.1 0.135 0.054 120 Example 13 compound 20 3.59 6.0 5.3 12.8 0.140 0.045 142 Comparative Example 1 compound A 3.48 3.6 3.3 7.6 0.141 0.044 85 Comparative Example 2 compound B 3.50 5.3 4.7 10.4 0.138 0.049 100

As a result of the experiment, the organic light emitting device including the compound of the present invention as a dopant, compared to the organic light emitting device including Comparative Examples 1 and 2, exhibited characteristics of equal or lower voltage, excellent efficiency, and , it is possible to provide an organic light emitting device having excellent color purity and long lifespan.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements of those skilled in the art using the basic concept of the present invention defined in the following claims are also made according to the present invention. falls within the scope of the rights of

Claims (7)

A compound represented by Formula 1 below:
[Formula 1]

here,
n and m are the same as or different from each other and are each independently 0 or 1,
Y ₁ is B, N, P=0 or P=S;
X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of N, C(R ₂ ), B and Si(R ₃ ),
X ₃ to X ₅ are the same as or different from each other, and are each independently a single bond, N(R ₄ ), C(R ₅ )(R ₆ ), O, S, and Si(R ₇ )(R ₈ ) A group consisting of is selected from,
Cy ₁ to Cy ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms,
R ₁ to R ₈ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,
The substituents of Cy ₁ to Cy ₄ and R ₁ to R ₈ are the same as or different from each other, and are each independently selected from hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, and an alkene having 2 to 30 carbon atoms. Nyl group, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms One selected from the group consisting of an alkyl group, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms It may be substituted with the above substituents. According to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 2 or Formula 3 below:
[Formula 2]

[Formula 3]

here,
n, m, Y ₁ , X ₁ to X ₅ , Cy ₁ to Cy ₄ and R ₁ are as defined in claim 1,
X ₆ and X ₇ are the same as or different from each other, and are each independently a single bond, N(R ₉ ), C(R ₁₀ ) (R ₁₁ ), O, S, and Si(R ₁₂ ) (R ₁₃ ). is selected from,
CY ₅ and CY ₆ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms;
R ₉ to R ₁₃ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,
The substituents of Cy ₅ , Cy ₆ and R ₉ to R ₁₃ are the same as or different from each other, and are each independently selected from hydrogen, cyano group, nitro group, halogen group, hydroxy group, C1-30 alkyl group, and C2-30 alkene group. Nyl group, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms One selected from the group consisting of an alkyl group, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms It may be substituted with the above substituents. According to claim 1,
The compound represented by Formula 2 is a compound represented by Formula 4 or Formula 5 below:
[Formula 4]

[Formula 5]

here,
n, m, Y ₁ , X ₁ to X ₆ , Cy ₁ , Cy _2, Cy ₅ and R ₁ are as defined in claim 2,
o, p and q are the same as or different from each other, and each independently represents an integer from 0 to 4;
r is an integer from 0 to 2;
Z ₁ is selected from the group consisting of O, S, N(R ₁₈ ) and C(R ₁₉ )(R ₂₀ );
R ₁₄ to R ₂₀ are the same as or different from each other, and each independently represents hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon number. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,
The substituents of R ₁₄ to R ₂₀ are the same as or different from each other, and are each independently hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a carbon atom 2 to 24 alkynyl group, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, and 1 to 30 carbon atoms may be substituted with one or more substituents selected from the group consisting of an alkoxy group, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms have. According to claim 1,
The compound represented by Formula 3 is a compound represented by Formula 6 below:
[Formula 6]

here,
n, m, Y ₁ , X ₁ to X ₇ , Cy ₁ , Cy _2, Cy _5, Cy ₆ and R ₁ are as defined in claim 2,
s and t are the same as or different from each other, and are each independently an integer of 0 to 3,
R ₂₁ and R ₂₂ are the same as or different from each other, and are each independently hydrogen, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom group. 2 to 30 alkynyl group, substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 1 to 30 carbon atoms 30 heteroaryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is selected from the group consisting of a cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms, and is bonded to adjacent substituents to form a ring. can do,
The substituents of R ₂₁ and R ₂₂ are the same as or different from each other, and are each independently hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a carbon atom group having 2 to 24 carbon atoms. alkynyl group, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, and 1 to 30 carbon atoms may be substituted with one or more substituents selected from the group consisting of an alkoxy group, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms have. a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode,
An organic electroluminescent device in which at least one of the one or more organic material layers contains the compound according to claim 1. According to claim 5,
The organic material layer is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. According to claim 5,
The organic material layer is an organic electroluminescent device that is a light emitting layer.